Good catch on Mrs. Oh's name — I missed that myself. The actor playing her is MADtv's Bobby Lee but it's impossible to tell if the character is supposed to be a man crossdressing, or the joke is it's obviously a male actor crossdressing (similar to Mrs. Whitehead.)
The timeline could add up. Annyong was arrested in "Red Hairing" and the editing implies it is 2012, but if it were earlier he could have been put into Lucille's prison in some way... but this is a very long shot.